Spin-Carrying Benzoquinone Derivatives

Several 1,4-benzoquinone derivatives carrying oxy-TEMPO radical(s) at the 2-position or 2,5-positions were found to give black crystals by recrystallization from pale yellow solutions and it was revealed from their crystal structures that unusual single-component CT complexes were formed, in which a...

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Bibliographic Details
Published in:Journal of organic chemistry 2009-12, Vol.74 (24), p.9345-9350
Main Authors: Nakatsuji, Shin’ichi, Nobusawa, Mitsunori, Suzuki, Hideto, Akutsu, Hiroki, Yamada, Jun-ichi
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Free radicals chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Reactivity and mechanisms
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Summary:Several 1,4-benzoquinone derivatives carrying oxy-TEMPO radical(s) at the 2-position or 2,5-positions were found to give black crystals by recrystallization from pale yellow solutions and it was revealed from their crystal structures that unusual single-component CT complexes were formed, in which a nitroxide moiety plays the roll of a donor part and a 1,4-benzoquinone group of the same molecule works as an acceptor part, respectively. On the contrary, no CT formation was found for the derivatives carrying oxy-TEMPO radicals at 2,6-positions and one of the TEMPO groups contributes to a CT formation in a 1,4-benzoquinone derivative carrying amino-TEMPO radicals at 2,5-positions derived from fluoranil, while the other one has a close oxygen-to-oxygen contact with another neighboring molecule to give a very large exchange coupling of J/k B = −154 K.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo902007m